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The Research About The Synthesis Method Of Peroxides

Posted on:2013-10-24Degree:MasterType:Thesis
Country:ChinaCandidate:Y H LiuFull Text:PDF
GTID:2231330395454078Subject:Organic Chemistry
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Peroxides such as artemisinin and Yingzhaosu are widely concerned by organicchemists and pharmacologists because of their distinctive antimalarial activity. At present,there are adequate studies proving that peroxy functional groups are the key to thesecompounds with antimalarial activity. Besides, peroxides as oxidant can be used in oxidationreaction. Therefore, preparing for new peroxides, developing new synthetic method forperoxides, applying them to the research of antimalarial activity and some oxidation reactionshave important theoretical significance and application potential.Since the1970s, when natural product artemisinin with excellent antimalarial activitywas found to have peroxy structure and its peroxy bond was the key of its antimalarial activity,organic peroxides has begun to cause high attention from the pharmaceutical field andbiological field, and aroused great interest from synthetic chemists. So far, more than600kinds of compounds containing peroxy bond have been extracted from natural plants andmarine organisms. At the same time, total synthesis research of these compounds has beencarried out, and various structure types of cyclic peroxides have been synthesized. Thesecompounds mainly consist of1,2-dioxanes,1,2,4-trioxanes,1,2,4-trioxolanes,1,2,4-trioxepanes and1,2,4,5-tetroxanes structures.Due to limited types of natural sources organic peroxides, synthesis of these compoundsneed to introduce or build peroxy bonds into the molecules. As bond energy of peroxy bond islow, rather unstable, and very sensitive to reaction conditions or reagents commonly used inmany organic synthesis, the development of effective synthesis method of these compounds isof much necessity. In particular, the method of utilizing some simple and easy to find rawmaterials to synthesis some new peroxides is one of today’s active research topics.Organic gem-dihydroperoxides (DHPs) have good biological and pharmaceuticalproperties, such as antiparasitic and antimicrobial activity. They are also used in allergens,anti-fungal, anti-tumour pharmaceuticals and inhibitors of enzymes. DHPs can also be used asoxidant in epoxidation, vulcanization oxidation reaction, synthesis of oligodeoxynucleotide,and it can also be used as initiating agent for molecular polymerization. In addition, these compounds are intermediates for synthesizing1,2,4,5-tetraoxacycloalkanes,1,2,4-trioxanes,1,2,4,5,7,8-hexaoxonanes, macrocyclic endoperoxides, and series of acylic analogues withsimilar functional groups. In this paper, using aldehydes and ketones as raw material, cheapand easy to get peroxide(30%) as oxidant, we have synthesized a series of organicgem-dihydroperoxides under room temperature.1,2,4-Trioxane is one of the cyclic peroxides which have antimalarial activity. Becausethe application of this compounds is more and more widely, indepth study and develop andbuild simple synthesis method for it will promote the developments in organic synthesis andmedicine field. We use β-hydroperoxy and aldehydes or ketones as raw material, in thepresence of a catalytic amount of magnetic nanoparticles γ-Fe2O3@SiO2-BpimCl-FeCl3,andsynthesis many kinds of1,2,4-trioxanes.In summary, we build a simple method for synthesis of gem-dihydroperoxides and cyclicperoxides1,2,4-trioxane derivatives. This method has the advantage of mild reactioncondition, simple operation, short time reaction, and high productivity. I believe it willpromote the development of organic cyclic peroxides.
Keywords/Search Tags:Artemisinin, Peroxides, Antimalarial activity, gem-Dihydroperoxides, 1,2,4-Trioxane derivatives, Magnetic nanoparticles
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